Climatic and micro-climatic phenomena such as summer heat waves and Urban Heat Island (UHI) are increasingly endangering the city’s livability and safety. The importance of urban features on the UHI effect encourages us to consider the configuration of urban elements to improve cities’ sustainability and livability. Most solutions are viable when a city redevelops and new areas are built to focus on aspects such as optimum design and the orientation of building masses and streets, which affect thermal comfort. This research looks beyond outdoor thermal comfort studies using UHI data and geoprocessing techniques in Tallinn, Estonia. This study supposes that designing urban canyons with proper orientation helps to mitigate the UHI effect by maximizing outdoor thermal comfort at the pedestrian level during hot summer days. In addition, optimizing the orientation of buildings makes it possible to create shaded and cooler areas for pedestrians, reducing surface temperature, which may create more comfortable and sustainable urban environments with lower energy demands and reduced heat-related health risks. This research aims to generate valuable insights into how urban environments can be designed and configured to improve sustainability, livability, and outdoor thermal comfort for pedestrians. According to the study results, researchers can identify the most effective interventions to achieve these objectives by leveraging UHI data and geoprocessing techniques and using CFD simulations. This evaluation is beneficial in guiding urban planners and architects in proposing mitigation solutions to enhance thermal comfort in cities and creating suitable conditions for approved thermal comfort levels. Results of the study show that in the location used for the survey, Tallinn, Estonia, the orientation of West-East offers the optimum level of comfort regarding thermal comfort and surface temperature in the urban environment.